Caleb Brewster
Caleb Brewster (12 September 1747 – 13 February 1827) was a Lieutenant in the Continental Army and a member of the Culper Ring in New York City during the American Revolutionary War. Brewster served as the courier from George Washington's intelligence chief Benjamin Tallmadge to the Culper Ring leader Abraham Woodhull in Setauket, Long Island, being signalled whenever Anna Strong hung a black petticoat from her clothing line. Brewster was also used in several secret missions involving infiltration or ambushes, and Brewster proved himself to be a very useful agent. Biography Caleb Brewster was born on 12 September 1747 in Setauket, New York, and he was the great-grandson of the first minister of the old church in the town. Brewster worked as a merchant before the American Revolution, with his travels taking him to Greenland on one occasion in 1776. When the war broke out, he joined the patriots under his childhood friend Benjamin Tallmadge, and he recruited his other old friend Abraham Woodhull into the patriot cause in the autumn of 1776. Brewster served as Tallmadge's courier to the Culper Ring (Woodhull's spy network), with Anna Strong giving him signals. In November 1776, he found out from Woodhull that 1,500 Hessians were waiting to embark for Trenton, New Jersey, after Woodhull conversed with a Hessian soldier outside of King's College while enjoying sauerkraut with them; this information would have helped George Washington's victory at the Battle of Trenton, but General Charles Scott threw out the document before the document could reach Washington due to Woodhull being an unverified source. However, Washington discovered that the information was accurate, causing him to appoint Tallmadge as his new intelligence chief and dismissing Scott, who was sent to the front. Brewster would carry information from Woodhull to Tallmadge, learning tradecraft from Washington's spymaster Nathaniel Sackett, including "sympathetic stain" (invisible ink), a finger-clenching device to determine if a person is telling the truth (by reading the heart rate), and writing on hard-boiled eggs. Woodhull was uncooperative at times, and Washington made foolish choices on other occasions, complicating matters. When Woodhull was arrested in New York City in December 1777, Brewster decided to break him out of prison by infiltrating the city in the Turtle, the first submarine in history. Brewster took the submarine through New York Harbor and landed at the dock, where he was accosted by British soldiers. He was taken onto the dock, but not before he was able to set a timer on the submarine that exploded as British soldiers searched it. Brewster then shook off the one soldier on the dock and fled, and he headed to the Holy Ground brothel. Brewster snuck into a tent where a prostitute was having sex with a British officer, and he left the prostitute some gold to bribe her as he stole the officer's coat. Brewster then proceeded to shave, and he was able to put on an act that made Inspector-General Joseph Innes believe that he was a cruel officer who would interrogate Woodhull. Brewster was mad when Woodhull was ungrateful for his efforts, as Woodhull wanted Hewlett to vouch for him and get him out of prison without drawing suspicion to him, but Woodhull decided to use Brewster in another way, asking him to convince Robert Townsend to join the Culper Ring. Brewster succeeded in telling him how to use the invisible ink, and Townsend agreed to join the ring as "Culper, Jr.". Later in the war, Brewster's identity was revealed by double agent William Heron on 4 February 1781, but he managed to evade capture by the British until the end of the war. After the war, he became a blacksmith and died in 1827 in Black Rock, Connecticut. Category:1747 births Category:1827 deaths Category:American spies Category:Americans Category:Spies Category:English-Americans Category:Protestants Category:Soldiers Category:American soldiers Category:Merchants Category:American merchants Category:People from New York Category:People from Long Island Category:People from Setauket Category:People from Black Rock, Connecticut Category:People from Connecticut Category:Patriots